In the oil industry throughout its supply chain there are several problems that cause daily losses of millions caused by falls in crude oil production, as well as failures caused by wear of pipelines and equipment, predominantly from corrosion problems, because of this is that globally the investigations are aimed at generating solutions through a variety of methods to minimize such problems.
Corrosion is a phenomenon that causes millions in losses in the oil industry, because it occurs in virtually all oil production chain from farm to processing it.
Corrosion is considered the progressive wear of a metallic material due to its interaction with the surrounding environment.
Corrosion taking place in environments characteristic of the petroleum industry can be caused by a large number of pollutants, among which hydrogen sulfide, carbon dioxide, organic acids, inorganic salts such as sodium chloride, ammonium cyanide, scales as barium sulfate, calcium carbonate, strontium sulfate and calcium sulfate and hydrochloric acid, among others, these pollutants cause loss of metallic material by uniform corrosion and pitting which can lead to serious accidents.
The corrosion phenomenon is also commonly found in transportation and storage of products derived from oil refining as gasoline without desulfurize, gasoline with low sulfur, diesel, alkylated gasoline, jet fuel, diesel and methyl tert butyl ether, from others.
The main damage caused by internal corrosion is uniform wear of the material, mainly due to the formation of iron sulfides and chlorides.
For the particular case of the services area, especially in cooling systems, the high concentration of divalent ions such as calcium and magnesium in the water used is the main factor of wear of piping and equipment, and accidents due to pitting corrosion. In this regard, it is important to note that both globally and in Mexico there is a tendency of increasing the production of heavy crude oils, which generally have a higher content of pollutants, as well as environmental regulations that increasingly restrict the use of water, the concentration of divalent ions such as calcium and magnesium is increased by evaporation of water lost to the environment, caused by heat exchange with other process fluids.
Because of this, the global trend in the area of chemicals is the development of corrosion inhibitors with a greater degree of versatility, capable of controlling the corrosion levels despite significant increases in contaminants in crude oil, fuel and water used in the process, which imparts a more aggressive characteristic.
Gemini surfactants are a family that is characterized by having in their molecules at least two hydrocarbon chains and two hydrophilic or polar groups:
whereas the conventional surfactant molecules contain one or two hydrocarbon chains attached to the same polar group.
In this regard, most of the gemini surfactants in their molecules have a hydrocarbon chain, a polar group, a short hydrocarbon chain that acts as a bridge or spacer, a second polar group and a hydrocarbon chain.
The first synthesis of gemini surfactants was announced in 1971 by C. A. Bunton, L. Robinson, J. Schaak, M. F. Stam, University of California, who called them dication detergents. These researchers used gemini cationic surfactants as catalysts for certain reactions of nucleophilic substitution. The successive names taking these substances were bis-quaternary ammonium surfactants, dimeric surfactants, gemini surfactants and siamese surfactants.
In most of the gemini surfactants, the polar groups are ionic (cationic, anionic and, less frequently, amphoteric), but also synthesized surfactants with nonionic polar groups formed by polyethers. In the pioneering work of Bunton, Robinson, Schaak and Stam, the short hydrocarbon chain that acts as a bridge and linking the two parts of surfactant, each of which is consisting of a polar group, in this case a cation and a lipophilic chain.
Representative examples of new processes for obtaining gemini surfactants are:                U.S. Pat. No. 5,945,393 (A), issued Aug. 31, 1999, discloses obtaining gemini non-ionic surfactants based on alkyl phosphonates or sulfonates or alkyl aryl polyethers, and its application in the formulation of detergents and personal hygiene products.        U.S. Pat. No. 5,952,290 (A), issued Sep. 14, 1999, discloses obtaining base anionic gemini surfactants alkyl amides or alkyl aryl sulphonated and its application in the formulation of detergents and personal hygiene products.        U.S. Patent Publication No. 2003/078176 (A1), published Apr. 24, 2003, discloses obtaining surfactants with long chain alcohols and polyether derivatives of ethylene oxide and its application in detergent formulation.        U.S. Patent Publication No. 2003/078182 (A1), published Apr. 24, 2003, discloses obtaining base compositions of gemini surfactants 1,2-epoxy-alkane where the alkyl groups may be linear or branched, polyols derived from ethylene oxide and its application in detergents.        U.S. Patent Publication No. 2009/054368 (A1), published Feb. 26, 2009, discloses obtaining gemini surfactants quaternary amine base substituted alkyl or aryl groups such as pyrene and its application in the controlled release of active biological agents such as nucleic acids.        
Representative examples of corrosion inhibitors used in acid environments of the oil industry are:                U.S. Pat. No. 3,623,979 (A), issued Nov. 30, 1971, relates to obtaining a base compound aminoalkyl-2-alkyl imidazolines and their use as corrosion inhibitors for ferrous metals in acidic characteristic of the oil industry. The efficiency of corrosion inhibition of these compounds was evaluated by gravimetric techniques.        U.S. Pat. No. 3,629,104 (A), issued Dec. 21, 1971, relates to the procurement of organic acid salts of compounds derived base 1-aminoalkyl-2-alkyl imidazolines and their use as corrosion inhibitors for ferrous metals in acidic characteristic of the oil industry. The efficiency of corrosion inhibition of these compounds was evaluated by gravimetric techniques        U.S. Pat. No. 3,390,085 (A), issued Jun. 25, 1968, relates to a mixture containing an imidazoline salt prepared from the reaction of a fatty acid having 6 to 18 carbons with imidazoline selected from the group consisting of 1-aminoalkyl-2-alkyl-imidazoline and 1-hydroxyalkyl-2-alkyl imidazolines and their application as corrosion inhibitors in acidic characteristic of the oil industry.        U.S. Pat. No. 4,388,214 (A), issued Jun. 14, 1983, relates to corrosion inhibitors synthesized from the reaction of imidazoline salts and imidazolines with sulfur. These compounds are particularly useful for inhibiting corrosion of metal containers caused by carbon dioxide and hydrogen sulfide during transport and storage of crude oil.        U.S. Pat. No. 5,062,992 (A), issued Nov. 5, 1991, relates to a corrosion inhibiting formulation for oil and water systems, wherein the formulation is resistant to sludge formation and tends to stabilize oil in water. The corrosion inhibitor includes an imidazoline dissolved in an aromatic solvent, a 2-hydroxyalkyl carboxylic acid and glycol. The imidazoline is preferably prepared from the reaction of a long chain fatty acid and a polyamine.        
Representative examples of corrosion inhibitors used in piping, tanks and other combustible handlers are:                U.S. Pat. No. 4,214,876 (A) (Corrosion inhibiting composition), issued Jul. 29, 1980, relates to the development of a formulation of the corrosion inhibition for ferrous metals exposed to hydrocarbon fuels comprising 75-95 weight percent of an unsaturated aliphatic carboxylic acid 16 to 18 carbons and 5 to 25 weight percent of succinic acid with a monoalkenyl chain in the range of 8 to 18 carbons, and use of a solvent hydrocarbon.        U.S. Pat. No. 4,509,951 (A) (Corrosion inhibitor for alcohol-based fuels and gasoline-alcohol mixtures), issued Apr. 9, 1985, relates to the development of a formulation of the corrosion inhibition for ferrous metals exposed to liquid fuels based in alcohol or gasoline-alcohol mixtures consisting of aliphatic carboxylic acid polyunsaturated with 18 carbons, and the reaction product of a polyamine with an alkenyl monounsaturated carboxylic acid or aliphatic or alkenyl succinic anhydride from 8 to 30 carbons.        U.S. Pat. No. 4,511,366 (A) (Liquid fuels and concentrates containing corrosion inhibitors), issued Apr. 16, 1985, relates to the development of a formulation of the corrosion inhibition for ferrous metals exposed to liquid alcohol-based fuel or gasoline-alcohol mixtures composed of an aliphatic carboxylic acid polyunsaturated 16 to 18 carbons and an alkenyl polyamine.        U.S. Pat. No. 4,737,159 (A) (Corrosion inhibitor for liquid fuels), issued Apr. 12, 1988, relates to the development of a formulation of the corrosion inhibition for ferrous metals exposed to liquid hydrocarbon fuels comprising 35-70 weight percent of monoalkenyl succinic acid with a chain from 8 to 18 carbons and 30 to 65 weight percent of an aliphatic or cycloaliphatic amine containing from 2 to 12 carbons and solvents, aromatic hydrocarbon compounds and alcohols of 1 to 4 carbons.        
Representative examples of corrosion inhibitors used in cooling systems include:                U.S. Pat. No. 3,974,090 (A), issued Aug. 10, 1976, relates to obtaining alkali metal phosphonates and their application as corrosion inhibitors for cooling systems that use water with high content of divalent ions such as calcium and magnesium.        U.S. Pat. No. 4,003,842 (A), issued Jan. 18, 1977, relates to obtaining base compounds phosphonates, sulfonates and carboxylates derived from aliphatic alcohols and polyether derivatives of ethylene oxide and its application as corrosion inhibitors in cooling systems.        WO 00/30985 (A2), published on Jun. 2, 2000, relates to obtaining amino-phosphonates based compounds and use as corrosion and fouling inhibitors in cooling systems.        U.S. Pat. No. 4,234,511 (A), issued Nov. 18, 1980, relates to obtaining base compounds di-alkyl amino phosphonates and their application as corrosion inhibitors in aqueous systems and cooling towers.        U.S. Pat. No. 6,215,013 (B1), issued Apr. 10, 2001, relates to the obtaining of bisphosphonic acids and derivatives and their use as corrosion inhibitors in cooling systems present in the chemical industry.        U.S. Pat. No. 6,572,789 (B1), issued Jun. 3, 2003, relates to obtaining oligomers phosphine-succinic acid and their application as corrosion inhibitors in aqueous systems such as cooling towers.        